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88899-55-2

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88899-55-2 Usage

Description

Bafilomycin A1 is a fungal metabolite that has been found in Streptomyces and has diverse biological activities. It is an inhibitor of vacuolar H+-ATPases (V-ATPases; Ki = 0.5 nM in N. crassa vacuolar membranes) and is greater than 1,000-fold selective for V-ATPases over Na+/K+-, Ca2+-, and H+-ATPases. Bafilomycin A1 (100 nM) inhibits autophagosome maturation and protein degradation in H-4-II-E cells. It inhibits chloroquine-induced apoptosis in primary cerebellar granule neurons (CGNs) but not chloroquine-induced inhibition of macroautophagy. Bafilomycin A1 (100 nM) reduces viral yield in the culture supernatant of Vero E6 and Huh7 cells, as well as HEK293T cells expressing human angiotensin-converting enzyme 2 (ACE2), infected with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). It also reduces lung RNA copy numbers and viral pneumonia in ACE2 transgenic mice infected with SARS-CoV-2 when administered at a dose of 0.1 mg/kg.

Chemical Properties

white to off-white powder

Uses

Different sources of media describe the Uses of 88899-55-2 differently. You can refer to the following data:
1. Bafilomycin A1 is a member of a potent family of macrocyclic lactones with broad spectrum biological activity, including activity against bacteria, yeast, fungi, nematodes, insects and tumour cell lines. Bafilomycin A1 is an inhibitor of vacuolar-type ATPase.
2. A macrolide antibiotic and potent and selective inhibitor of vacuolar-type (v-type) H+ ATPase
3. Bafilomycin A1 is a specific potent inhibitor of vacuolar ATPases.It is used as an antibacterial, antifungal, antineoplastic and an immunosuppressive. It prevents maturation of autophagic vacuoles by inhibiting fusion between autophagosomes and lysosomes and is a macrolide antibiotic and potent and selective inhibitor of vacuolar-type H+ ATPase (V-ATPase).

Definition

ChEBI: The most used of the bafilomycins, a family of toxic macrolide antibiotics derived from Streptomyces griseus.

General Description

A macrolide antibiotic that acts as a specific inhibitor of vacuolar-type H+-ATPase (V-type; Ki = 500 pM). A valuable tool for distinguishing among different types of ATPases. Blocks lysosomal cholesterol trafficking in macrophages and is known to interfere with pH regulation in brain cells. Exhibits cytotoxic effects on a number of cell lines in a cell viability assay. Reported to selectively inhibit β-secretase, an enzyme involved in the processing of amyloid precursor protein (APP). The InSolution format with a purity of ≥97% by HPLC in 90% DMSO is also available (Cat. No. 508409).

Biological Activity

Highly potent, selective inhibitor of vacuolar H + -ATPases (IC 50 = 500 pM as measured in chromaffin granule membranes). Selective over other ATP hydrolyzing enzymes such as F-ATPases, Ca 2+ -ATPases, Na + /K + -ATPases and plasma membrane H + -ATPases.

Biochem/physiol Actions

Bafilomycin A1 is a macrolide antibiotic. Bafilomycin A1 acts as a potent and selective inhibitor of vacuolar-type H+-ATPase.

References

1) Werner?et al.? (1984) Metabolic products of microorganisms. Bafilomycins, a new group of macrolide antibiotics. Production, isolation, chemical structure and biological activity; J. Antibiot.,?37?110 2) Drose and Altendorf? (1997)?Bafilomycins and concanamycins as inhibitors of V-ATPase and P-ATPase;?J. Exp. Biol.,?200?1 3) Yamamoto?et al. (1998)?Bafilomycin A1 prevents maturation of autophagic vacuoles by inhibiting fusion between autophagosomes and lysosomes in rat hepatoma cell line, H-4-II-E cells;?Cell Struct. Func.,?23?33

Check Digit Verification of cas no

The CAS Registry Mumber 88899-55-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,8,8,9 and 9 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 88899-55:
(7*8)+(6*8)+(5*8)+(4*9)+(3*9)+(2*5)+(1*5)=222
222 % 10 = 2
So 88899-55-2 is a valid CAS Registry Number.
InChI:InChI=1/C35H58O9/c1-19(2)32-24(7)27(36)18-35(40,44-32)26(9)31(38)25(8)33-28(41-10)14-12-13-20(3)15-22(5)30(37)23(6)16-21(4)17-29(42-11)34(39)43-33/h12-14,16-17,19,22-28,30-33,36-38,40H,15,18H2,1-11H3/b14-12+,20-13+,21-16+,29-17-/t22-,23+,24-,25-,26-,27+,28-,30-,31+,32+,33+,35+/m0/s1

88899-55-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name bafilomycin A1

1.2 Other means of identification

Product number -
Other names (3Z,5E,7R,8S,9S,11E,13E,15S,16R)-8-Hydroxy-16-((1S,2R,3S)-2-hydroxy-1-methyl-3-((2R,4R,5S,6R)-tetrahydro-2,4-dihydroxy-5

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:88899-55-2 SDS

88899-55-2Relevant articles and documents

Diastereoselective Aldol Reactions of β-Silyloxy Ethyl Ketones. Application to the Total Synthesis of Bafilomycin A1

Evans, David A.,Calter, Michael A.

, p. 6871 - 6874 (1993)

Studies directed toward the C17-C18 aldol bond construction in the macrolide antibiotic bafilomycin A1 are described.The effect of the β-substituent in the aldol reactions of α-unsubstituted enolates is documented for various model compounds.The stereoselectivity of this process is critically dependent on the C21 and C23 oxygen protecting groups.Application of this methodology to the synthesis of bafilomycin A1 is reported.

Total synthesis of (-)-bafilomycin A1

Scheidt, Karl A.,Bannister, Thomas D.,Tasaka, Akihiro,Wendt, Michael D.,Savall, Brad M.,Fegley, Glenn J.,Roush, William R.

, p. 6981 - 6990 (2007/10/03)

A highly stereoselective total synthesis of (-)-bafilomycin A1, the naturally occurring enantiomer of this potent vacuolar ATPase inhibitor, is described. The synthesis features the highly stereoselective aldol reaction of methyl ketone 8b and

Total synthesis of (-)-bafilomycin A1: Application of diastereoselective crotylboration and methyl ketone aldol reactions

Scheldt, Karl A.,Tasaka, Akihiro,Bannister, Thomas D.,Wendt, Michael D.,Roush, William R.

, p. 1652 - 1655 (2007/10/03)

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